It depends on the bank you are using, most of them prefer long term income (which is more reliable to them and safer) but if you can show proof of income history being used as short term that might help too.

I want to buy a property from an investment perspective, I was wondering which out of these two cities would be preferable in terms of ease of renting (rent per month and the time it takes to rent it out). 

Same builder, same house, in same neighborhood for example could back to a busy main street in the entrance of the neighborhood, could face West where people prefer East facing, be the house that everyone drives by and lights shine in the front windows when you enter the neighborhood, could back to power lines in the back of the neighborhood, could be next to the community pool, could be on a corner with a bigger lot, and a host of other factors go into pricing....not just size.The 3 main sources that most sellers use for size are tax roll, appraiser, or builder's plan. 

Many syndications have the manager taking 20-30% AFTER the partners are paid their preferred share.The manager would still be compensated for their other duties like managing rehabs and leases at fair market rates.

The oldest are now 39, married with kids - once said they would prefer to rent, uber instead of buy a car and work from a coffeeshop, now they are starting families and that changes everything.

It's really up to your preference, but if you do this then you are going to be getting door knocks at 3am in the morning to fix toilet clogs.

Can you maybe give some insight on why you’d choose Indianapolis and any preferred agents, contractors, lenders, etc that I could reach out to would be awesome!

I would prefer more than one unit but, one would be alright.

Some people like the flipping business model, I just prefer buy & hold. 

I’m going to go against the grain and say you should learn how to find an off market deal.The method will depend on budget and preference, but once you realize if you buy good enough deals you don’t need down payments that’s a game changer.